Cisplatin and other platinum anticancer drugs are known to react readily with DNA; the primary target within DNA is the N7 atom of guanine followed by the N7 atom of adenine.  We have investigated how the size and shape of the amine ligands attached to the platinum atom affect the reaction with 5'-AMP realative to 5'-GMP.  In general, we have found that reaction of adenine is considerably slower than reaction with guanine.  For one platinum compound, [Pt(Me5dien)(NO3)]+, where Me5dien = N,N,N',N',N'-pentamethyldiethylenetriamine, we found that reaction with 5'-AMP was very slow compared to reaction with 5'-GMP, and products due to N1-coordinated 5'-AMP and N7-coordinated 5'-AMP were observed in nearly equal amounts as determined by NMR spectroscopy.  Thus, the size of the Me5dien ligand appears to interfere with the reaction at the N7 position due to the size of the amino group at C6 of adenine.

Reaction of platinum(II) diamine and triamine complexes with adenosine 5'-monophosphate

248th National Meeting (2014)

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